Find hotels in Highland Beach, MD from ₩107,034

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Compare 1,224 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Highland Beach hotels

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is ₩176,996
₩196,466 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Annapolis East-Kent Island by IHG
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very Good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is ₩291,876
₩354,922 total
includes taxes & fees
Sep 1 - Sep 2
Inn at Haven Harbour
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Excellent location"
The price is ₩151,603
₩168,280 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Kent Narrows Inn
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Great place to stay"
The price is ₩140,175
₩154,195 total
includes taxes & fees
Sep 7 - Sep 8
St Michaels Inn
Comfort Inn Conference Center
Dinner served, American cuisine

Comfort Inn Conference Center

2.5 star property
9.0 out of 10, Wonderful, (1019)
"Staff was nice and property was clean"
The price is ₩137,973
₩155,910 total
includes taxes & fees
Sep 1 - Sep 2
Comfort Inn Conference Center
Microtel Inn & Suites by Wyndham Gambrills
Exterior

Microtel Inn & Suites by Wyndham Gambrills

2.0 star property
9.0 out of 10, Wonderful, (1011)
"Great place to stay "
The price is ₩107,034
₩122,019 total
includes taxes & fees
Sep 14 - Sep 15
Microtel Inn & Suites by Wyndham Gambrills
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (64)
"Good service and good options to enjoy the stays. "
The price is ₩236,059
₩320,986 total
includes taxes & fees
Sep 18 - Sep 19
Wylder Tilghman Island
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is ₩216,367
₩240,171 total
includes taxes & fees
Sep 1 - Sep 2
Mariners Motel
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (817)
"Conveniently located with overall great value."
The price is ₩136,189
₩151,169 total
includes taxes & fees
Sep 17 - Sep 18
Quality Inn
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (520)
"Beautiful property and lovely hosts."
The price is ₩250,861
₩285,981 total
includes taxes & fees
Aug 31 - Sep 1
Laurel Grove Inn on the South
SpringHill Suites by Marriott Annapolis
Free daily self-serve breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great place"
The price is ₩152,816
₩174,210 total
includes taxes & fees
Sep 3 - Sep 4
SpringHill Suites by Marriott Annapolis
Rod 'N' Reel Resort
Superior Studio Suite | Balcony

Rod 'N' Reel Resort

4.0 star property
8.4 out of 10, Very Good, (1003)
"Great place to stay."
The price is ₩186,891
₩235,322 total
includes taxes & fees
Sep 1 - Sep 2
Rod 'N' Reel Resort
Holiday Inn Express & Suites Annapolis by IHG
Free daily buffet breakfast

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1003)
"Great staff….property a bit “tired” but a very friendly staff working hard to make it comfortable. A decent value for location and price!"
The price is ₩153,304
₩174,766 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Annapolis by IHG
Anchored Inn at Hidden Harbour Marina
Front of property

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (446)
"The staff specifically Victoria was impeccable! "
The price is ₩249,606
₩284,559 total
includes taxes & fees
Sep 2 - Sep 3
Anchored Inn at Hidden Harbour Marina
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (414)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is ₩313,576
₩383,525 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Chesapeake Bay Beach Club
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (104)
"So friendly and professional service!"
The price is ₩285,702
₩314,272 total
includes taxes & fees
Sep 14 - Sep 15
The Tilghman Island Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (111)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is ₩229,154
₩305,336 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort
Sonesta ES Suites Annapolis
1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (869)
"Great room for a great price... Very friendly staff, too."
The price is ₩146,335
₩166,822 total
includes taxes & fees
Aug 31 - Sep 1
Sonesta ES Suites Annapolis
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1009)
"Very nice property new rooms "
The price is ₩109,138
₩124,418 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Annapolis
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (341)
"Our room overlooked the channel at Knapp's Narrows. The staff is friendly and helpful. We will definitely stay here again."
The price is ₩216,019
₩237,621 total
includes taxes & fees
Aug 29 - Aug 30
Knapps Narrows Marina & Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Highland Beach attractions

Chesapeake Bay Bridge
Chesapeake Bay Bridge

Chesapeake Bay Bridge

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

See properties in Chesapeake Bay Bridge
Navy-Marine Corps Memorial Stadium

Navy-Marine Corps Memorial Stadium

Catch an event at Navy-Marine Corps Memorial Stadium during your trip to Annapolis. Stroll along the waterfront or visit the shops in the area.

See properties in Navy-Marine Corps Memorial Stadium

Learn more about Highland Beach

This historic African American beach town offers peaceful Chesapeake Bay shorelines perfect for swimming and kayaking. Visit nearby Annapolis for its Naval Academy tours or explore Twin Oaks, Highland Beach's Frederick Douglass family summer home.

See all hotels in Highland Beach

Top Highland Beach Hotel Reviews

More cheap stays in Highland Beach

More cheap stays in Highland Beach

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd., Gambrills, MD
The price is ₩107,034 per night from Sep 14 to Sep 15
₩107,034
₩122,019 total
Sep 14 - Sep 15
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Where is the best place for a stay in Highland Beach?

Located 3.6 mi (5.8 km) from the heart of Highland Beach, Historic Inns of Annapolis is a top choice for your stay based on our traveler data. Two other options for your stay in the area are Graduate by Hilton Annapolis and Country Inn & Suites by Radisson, Annapolis, MD. See all available top hotels, or vacation rentals in Highland Beach.

If I need to cancel my hotel reservation in Highland Beach, will I receive a refund?

Yes, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Highland Beach.

Where can I learn more about changing or cancelling my trip to Highland Beach?

For additional details about rescheduling or cancelling your trip to Highland Beach, head over to our customer service page.

What is staying in Highland Beach like?

Visitors to Highland Beach are sure to find plenty to explore and enjoy. There are 1215 hotels and other accommodations in the surrounding area. Find out more about Highland Beach.

What should I see while I'm in Highland Beach?

Places to visit in the wider area include Bay Ridge Beach, Maryland Quiet Waters Park, and Annapolis Landing Marina. You'll also find Annapolis Maritime Museum and Ego Alley in the area. Check out what more to see and do in Expedia's Highland Beach guide.

What's the seasonal weather like in Highland Beach?

The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Highland Beach is 52 inches.